127061-11-4

Basic information

• Product Name: phenyl 1-thio-α/β-L-fucopyranoside
• Synonyms: phenyl 1-thio-α/β-L-fucopyranoside
• CAS NO: 127061-11-4
• Molecular Weight: 256.323
• Mol File: 127061-11-4.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: phenyl 1-thio-α/β-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 1-thio-α/β-L-fucopyranoside(127061-11-4)
• EPA Substance Registry System: phenyl 1-thio-α/β-L-fucopyranoside(127061-11-4)

Safety Data

• Hazardous Substances Data: 127061-11-4(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 
• 882-33-7 diphenyldisulfane 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 883884-80-8 1,2,3,4-tetra-O-acetyl-L-rhamnose 
• 6014-42-2 L-rhamnose 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 
• 940006-58-6 S-phenyl 2-O-acetyl-4-O-benzyl-3-O-(4-methoxybenzyl)-α-L-thiorhamnopyranoside 
• 3615-41-6 L-Rhamnose 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 940006-51-9 S-phenyl 3-O-(2-naphthylmethyl)-α-L-thiorhamnopyranoside 
• 940006-52-0 S-phenyl 3-O-benzyl-α-L-thiorhamnopyranoside 
• 940006-60-0 phenyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside 
• 940006-61-1 phenyl 2,3-di-O-benzyl-4-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside 
• 131087-36-0 phenyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-L-lyxo-hexopyranosid-4-ulose 
• 947256-89-5 phenyl 6-deoxy-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-L-mannopyranoside 
• 230948-99-9 C₂₀H₂₂O₅S 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions

Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-α-L-rhamnopyranose in combination with the two alcohols 1-adamantanol and L-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated that both lithium and the respective counterions are playing a role in the activation of trichloroacetimidate glycosyl donors at rt. Under these very mild conditions, the glycosylations are slow and completed in two to eight days. Depending on the counterion, the rate and yield of the reaction differs; however, the selectivity of all investigated lithium salts is deficient.

Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B

This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).

A concise synthesis of rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative α-glycosylation using disaccharide building blocks

A concise synthetic route to rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal co